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Dithiocarbamic acid mixed-valence copper complex as well as preparation and application thereof

A technology of dithiocarbamate and copper complexes, applied in the direction of copper organic compounds, drug combinations, chemical instruments and methods, etc.

Active Publication Date: 2020-08-18
江苏思默飞医疗科技有限公司
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Problems solved by technology

Currently, two combination regimens with moderate clinical activity, namely FOLFIRINOX (a therapeutic combination including oxaliplatin, 5-fluorouracil, leucovorin, and irinotecan) and nab-paclitaxel-gemcitabine, have been used as an option in patients with pancreatic cancer. treatment options, but they have distinct toxicity profiles such as neutropenia

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  • Dithiocarbamic acid mixed-valence copper complex as well as preparation and application thereof
  • Dithiocarbamic acid mixed-valence copper complex as well as preparation and application thereof
  • Dithiocarbamic acid mixed-valence copper complex as well as preparation and application thereof

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[0038] The technical solutions of the present invention will be further described in detail below in conjunction with specific embodiments.

[0039] 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), hydrazinecarbodithiomethyl ester, bis(pyridin-2-yl)methanone and CuBr 2 Available from Sigma-Aldrich. All other reagents and solvents were obtained from commercial sources and used without further purification.

[0040] (1) Synthesis and characterization of 2-(bis(pyridin-2-yl)methylene)hydrazinemethyl dithiosulfate ligand (HL):

[0041] Ligand 2-(bis(pyridin-2-yl)ylidene was synthesized by refluxing hydrazinecarbodithiomethyl ester (0.61 g, 5 mmol) and bis(pyridin-2-yl)methanone (0.92 g, 5 mmol) Methyl)hydrazinodithiomethyl ester (HL) to give a yellow solution. Yellow luminescent crystals of HL were formed by slow evaporation of the solvent at 4°C, yield 1.09 g (76%). Calculated value C 13 h 12 N 4 S 2(288.39): C, 54.14; H, 4.19 and N, 19.43. Found: C, ...

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Abstract

The invention discloses a dithiocarbamic acid mixed-valence copper complex as well as preparation and application thereof; the chemical formula of the copper complex is [CuII2(L)2(Br)2CuI(Br)], wherein HL is 2-(bis(pyridin-2-yl)methylene)hydrazine methyl methyl dithiosulfate. The preparation method of the copper complex is simple, and the target product dithiocarbamic acid mixed-valence copper complex has obvious fluorescence in a green region of 450-650 nm of a visible spectrum, is used for cancer cell imaging based on fluorescence and is used for preparing a cancer cell imaging fluorescent probe. The target product also has good anti-cancer activity and cancer cell metastasis resistance activity. Particularly, the target product provided by the invention can induce cancer cells with apoptosis resistance, such as pancreatic cancer cells and ferroptosis (cell death in a non-apoptotic form), effectively overcomes the occurrence of drug resistance, and has quite good application value.

Description

technical field [0001] The invention relates to copper complexes, in particular to a dithiocarbamic acid mixed-valent copper complex and its preparation method and application. Background technique [0002] Pancreatic cancer will become the second leading cause of cancer death in Western countries within the next decade, according to the survey. In contrast to the steadily increasing survival rates of most cancers, pancreatic cancer is slow to progress and currently has a 5-year survival rate of less than 5%. Surgical resection remains the only chance for long-term survival, but due to local vascular metastasis or invasion, less than one in five patients can be treated surgically. Therefore, the treatment of pancreatic cancer, especially advanced pancreatic cancer, largely depends on systemic chemotherapy. As early as 1996, gemcitabine monotherapy was approved by the FDA as the standard of care for pancreatic cancer, but its overall 5-year survival rate was only 6.7%, stil...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08C09K11/06A61P35/00G01N21/64
CPCC07F1/08C09K11/06A61P35/00G01N21/6428C09K2211/188C09K2211/1029G01N2021/6432
Inventor 苟峄李爱丽黄国锦姚冬
Owner 江苏思默飞医疗科技有限公司
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